Chloroform → N-propylamino-3-chloro propane hydrochloride

HRID 434400Notes

Reaction equation

HRID 434400 reaction equation
[CH2:1]([NH:4][CH2:5][CH2:6]CO)[CH2:2][CH3:3].[CH:9]([Cl:12])(Cl)[Cl:10]>S(Cl)(Cl)=O>[ClH:10].[CH2:1]([NH:4][CH2:5][CH2:6][CH2:9][Cl:12])[CH2:2][CH3:3]

Participants

4

Procedure

There was added to about 124 parts of the above N-propyl-3-amino propanol dissolved in 1194 parts of chloroform under an atmosphere of nitrogen and at a temperature of about 0° C., 189 parts of thionyl chloride at a rate which was sufficient to maintain the temperature of the resulting reaction mixture below 20° C. When the addition was complete, the solution was brought to reflux for 30 minutes. The reaction mixture was then quenched with excess ethanol and concentrated to provide a yellow viscous oil. There was obtained a quantitative yield of N-propylamino-3-chloro propane hydrochloride after the aforementioned yellow viscous oil was crystallized from ethanol in the form of a white crystalline solid; (M.P. 246°-247° C.).

Workup

  1. temperatureto maintain
  2. customthe temperature of the resulting reaction mixture below 20° C
  3. additionWhen the addition
  4. temperatureto reflux for 30 minutes
  5. customThe reaction mixture was then quenched with excess ethanol
  6. concentrationconcentrated
  7. customto provide a yellow viscous oil

Sources & evidence

ORD record
ord-fa9e4ad6765444948d2c818245acd2d3
Source dataset
uspto-grants-1983_08
Patent number
US04396728

Reaction notes

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